Background: The benefits of breastfeeding are widely known; however, continuation after returning to work (RTW) is not. We aimed to conduct a systematic review and meta-analysis to assess the prevalence of breastfeeding after RTW. The secondary objectives were to compare the economic statuses between continents. Method: PubMed, Cochrane Library, Base, and Embase were searched until 1 September 2020, and two independent reviewers selected the studies and collated the data. To be included, articles needed to describe our primary outcome, i.e., prevalence of breastfeeding after RTW. Results: We included 14 studies, analyzing 42,820 women. The overall prevalence of breastfeeding after RTW was 25% (95% CI, 21% to 29%), with an important heterogeneity (I2 = 98.6%)—prevalence ranging from 2% to 61%. Stratification by continents and by GDP per capita also showed huge heterogeneity. The Middle East had the weakest total prevalence with 10% (6% to 14%), and Oceania the strongest with 35% (21% to 50%). Despite the prevalence of breastfeeding in general increasing with GDP per capita (US$50,000 42%), the prevalence of non-exclusive breastfeeding follows more of a U-curve with the lowest and highest GDP per capita having the highest percentages of breastfeeding (US$50,000: 50%, versus <28% for all other categories). Conclusion: Breastfeeding after RTW is widely heterogeneous across the world. Despite economic status playing a role in breastfeeding after RTW, cultural aspects seem influential. The lack of data regarding breastfeeding after RTW in most countries demonstrates the strong need of data to inform effective preventive strategies.